A Diels-Alder strategy towards a benzonaphthopyranoquinone

Authors
Tapia, RA Alegria, L Valderrama, JA Cortes, M Pautet, F Fillion, H
Citation
Ra. Tapia et al., A Diels-Alder strategy towards a benzonaphthopyranoquinone, TETRAHEDR L, 42(5), 2001, pp. 887-889
Citations number
18
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
42
Issue
5
Year of publication
2001
Pages
887 - 889
Database
ISI
SICI code
0040-4039(20010129)42:5<887:ADSTAB>2.0.ZU;2-P
Abstract
Reaction of a suitably protected aryllithium derivative with citral, and su bsequent deprotection and cyclization was used to obtain dibenzopyran 5, a precursor of the tricyclic quinone 6. Diels-Alder reaction of 6 with 1,3-di methoxy-1-trimethylsilyloxy-1,3-butadiene 7 led to befizonaphthopyranoquino ne 8. The regioselectivity in the dienophilic partner is governed by the re mote oxygen of the pyran ring. (C) 2001 Elsevier Science Ltd. All rights re served.